Urinary tract infections (UTIs) are among the most common bacterial infections in outpatient clinical settings globally. Young healthy women are at highest risk of community-acquired UTI. While uncomplicated UTI is not life-threatening, it is associated with high morbidity and treatment costs. The pathogenesis of urinary tract infection in young healthy women is complex. It is influenced by a number of host biological and behavioural factors and virulence of the uropathogen. The infecting uropathogens in community-acquired UTI originate from the fecal flora, E.coli being the most predominant, accounting for 80-90% of these UTIs. Vaginal colonization with uropathogens, a pre-requisite for bladder infection may be facilitated by sexual intercourse, which has been shown to be a strong risk factor and predictor of UTI. While majority of studies have explored the association between heterosexual vaginal intercourse and UTI in healthy young women, the possible association with heterosexual receptive anal intercourse has not received adequate attention despite evidence of high prevalence globally. This paper presents two young healthy married women who had severe UTI following heterosexual anal intercourse and discusses possible association thereof. Understanding the risk factors for UTI and identification of possible predisposing conditions in a particular individual are important in guiding therapeutic approaches and preventive strategies. Cognisant of reportedly high prevalence of various sexual practices including receptive heterosexual anal intercourse and their impact on individuals’ health, details on sexual history should always be enquired into in young women presenting with genito-urinary complaints.